硒氰酸苯酯 | 2179-79-5

• 物质功能分类: 化学试剂 - 有机试剂 - 硒化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 硒氰酸苯酯
• 英文名称: phenyl selenocyanate
• 英文别名: selenocyanatobenzene；phenylselenocyanide
• CAS: 2179-79-5
• 化学式: C₇H₅NSe
• 分子量: 182.083
• InChiKey: NODWRXQVQYOJGN-UHFFFAOYSA-N

物化性质

• 沸点：
  116-117 °C/12 mmHg (lit.)
• 密度：
  1.484 g/mL at 25 °C (lit.)
• 闪点：
  >230 °F
• 溶解度：
  可与有机溶剂、四氢呋喃、二氯甲烷和乙腈混溶。
• 暴露限值：
  ACGIH: TWA 0.2 mg/m3NIOSH: IDLH 1 mg/m3; TWA 0.2 mg/m3
• 稳定性/保质期：
  避免氧化物接触，危险分解产品包括一氧化碳、二氧化碳、氧化氮、硒化氢和氰化氢，以及有毒的金属氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险等级：
  6.1
• 危险品标志：
  T,N
• 安全说明：
  S20/21,S28,S45,S60,S61
• 危险类别码：
  R23/25
• WGK Germany：
  3
• 海关编码：
  2929909090
• 包装等级：
  II
• 危险类别：
  6.1
• 危险品运输编号：
  UN 3440 6.1/PG 2
• 储存条件：
  储存地点应远离氧化剂，并确保容器密封，存放在干燥、阴凉处。

SDS

Name:	Phenylselenocyanate tech. 90+% (gc) Material Safety Data Sheet
Synonym:	None
CAS:	2179-79-5

Section 1 - Chemical Product MSDS Name:Phenylselenocyanate tech. 90+% (gc) Material Safety Data Sheet
Synonym:None

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
2179-79-5	PHENYLSELENOCYANATE	90.0+	unlisted

Hazard Symbols: T
Risk Phrases: 23/25 33

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Toxic by inhalation and if swallowed. Danger of cumulative effects.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
Poison by ingestion. The toxicological properties of this substance have not been fully investigated.
Inhalation:
The toxicological properties of this substance have not been fully investigated. Toxic if inhaled.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Never give anything by mouth to an unconscious person. Get medical aid immediately. Wash mouth out with water.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
Notes to Physician:
Antidote: None reported.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use carbon dioxide or dry chemical.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Clean up spills immediately, observing precautions in the Protective Equipment section. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Keep container tightly closed. Do not ingest or inhale. Use only in a chemical fume hood.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 2179-79-5: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: clear orange
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 116 - 117 deg C @ 12.00mbar
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: > 230 deg F (> 110.00 deg C)
Explosion Limits, lower: N/A
Explosion Limits, upper: N/A
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C7H5NSe
Molecular Weight: 182.08

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stability unknown.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide, selenium/selenium oxides.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 2179-79-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
PHENYLSELENOCYANATE - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION
Other No information available.

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.*
Hazard Class: 6.1
UN Number: 2810
Packing Group: II
IMO
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2810
Packing Group: II
RID/ADR
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2810
Packing group: II

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: T
Risk Phrases:
R 23/25 Toxic by inhalation and if swallowed.
R 33 Danger of cumulative effects.
Safety Phrases:
S 20/21 When using do not eat, drink or smoke.
S 28A After contact with skin, wash immediately with
plenty of water.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 2179-79-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 2179-79-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 2179-79-5 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

硒氰酸苯酯是一种硒基化剂，可通过苯硒基氯与三甲基氰化甲硅烷反应制得。其主要用途包括合成以下化合物：

• 苯硒醇酯
• 2-溴乙基苯基硒二溴化物
• α,α-二氧基-β-苯基硒腈
• β-烷氧基烷基苯基硒化物

反应信息

• 作为反应物：
  描述：

  硒氰酸苯酯 在 盐酸 、 锌 作用下， 生成 苯硒酚
  参考文献：
  名称：

  Behaghel; Hofmann, Chemische Berichte, 1939, vol. 72, p. 582,587

  摘要：

  DOI：
• 作为产物：
  描述：

  碘苯 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 硒氰酸苯酯
  参考文献：
  名称：

  通过 SnCl4 催化 (3+2)-环丙烷与硫代/硒氰酸酯的环加成反应合成硫代-/硒代吡咯啉

  摘要：

  通过 SnCl 4催化的 (3+2)-芳基硫代/硒氰酸酯与供体-受体环丙烷 (DAC) 的环加成反应，开发了一种高效的硫代/硒代吡咯啉合成方案。该协议使各种硫代/硒代吡咯啉的产率良好至极好。

  DOI：

  10.1002/ejoc.202100846
• 作为试剂：
  描述：

  6,7-二甲氧基-3,4-二氢异喹啉 在 sodium tetrahydroborate 、 sodium periodate 、 四氧化锇 、 lithium aluminium tetrahydride 、 Hoveyda-Grubbs catalyst second generation 、 硒氰酸苯酯 、 异丙基氯化镁 、 对甲苯磺酸 、 三乙胺 、 对苯醌 、 三甲基膦 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 甲醇 、 水 、 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran 、 丙酮 、 甲苯 、 苯 为溶剂， 反应 4.0h， 生成 (-)-protoemetinol
  参考文献：
  名称：

  2,3-二取代的苯并[α]喹诺唑烷生物碱的立体选择性合成的有效策略：（-）-protometetol的简明合成

  摘要：

  （-）-protometetol的立体选择性合成已通过九步从已知的均烯丙基胺完成。合成的关键步骤包括使用交叉复分解和酰胺烯酸酯诱导的ACR有效制备aza-Claisen重排（ACR）前体，然后进行酸催化的反硝化反应以精制苯并[α]喹啉嗪骨架和三个立体异构中心。这种独特的合成途径为2，3-二取代的苯并[α]喹喔啉的合成提出了统一而通用的策略。

  DOI：

  10.1016/j.tetlet.2014.12.030

文献信息

• General and Practical Formation of Thiocyanates from Thiols
  作者：Reto Frei、Thibaut Courant、Matthew D. Wodrich、Jerome Waser

  DOI：10.1002/chem.201406171

  日期：2015.2.2

  A new method for the cyanation of thiols and disulfides using cyanobenziodoxol(on)e hypervalent iodine reagents is described. Both aliphatic and aromatic thiocyanates can be accessed in good yields in a few minutes at room temperature starting from a broad range of thiols with high chemioselectivity. The complete conversion of disulfides to thiocyanates was also possible. Preliminary computational

  描述了一种使用氰基苯并齐多醇（on）高价碘试剂氰化硫醇和二硫化物的新方法。脂肪族和芳香族硫氰酸酯都可以在室温下以几分钟的高收率获得，其起始源是多种具有高化学选择性的硫醇。也可以将二硫化物完全转化为硫氰酸酯。初步的计算研究表明，硫氰酸根阴离子或自由基的氰化反应具有低能的一致过渡态。发达的硫氰酸酯合成方法在合成化学，化学生物学和材料科学中具有广泛的应用潜力。
• Direct Photocatalytic S–H Bond Cyanation with Green “CN” Source
  作者：Wei Guo、Wen Tan、Mingming Zhao、Lvyin Zheng、Kailiang Tao、Deliang Chen、Xiaolin Fan

  DOI：10.1021/acs.joc.8b00887

  日期：2018.6.15

  Herein we report a novel C–S bond cleavage and reconstruction strategy for the synthesis of thiocyanates through direct photocatalytic S–H bond cyanation from thiols and inorganic thiocyanate salts. In our strategy, the unprecedented example of cutting off C–S bond of SCN– to deliver the green “CN” sources is demonstrated. This transformation features nontoxic and inexpensive “CN” sources, available

  本文中，我们报道了通过硫醇和无机硫氰酸盐直接进行光催化的S–H键氰化反应合成硫氰酸盐的新颖的C–S键裂解和重构策略。在我们的战略，切断SCN的C-S键的前所未有的例子-提供绿色的“CN”来源证明。这种转化具有无毒且价格低廉的“ CN”源，可利用的起始原料，无金属/碱/配体/过氧化物，高步骤经济性和温和条件的特点。它导致了各种硫氰酸盐以及一些具有医学和生物活性的含硫氰酸盐分子的构建。
• Total Syntheses, Fragmentation Studies, and Antitumor/Antiproliferative Activities of FR901464 and Its Low Picomolar Analogue
  作者：Brian J. Albert、Ananthapadmanabhan Sivaramakrishnan、Tadaatsu Naka、Nancy L. Czaicki、Kazunori Koide

  DOI：10.1021/ja067870m

  日期：2007.3.1

  natural product that lowers the mRNA levels of oncogenes and tumor suppressor genes. In this article, we report a convergent enantioselective synthesis of FR901464, which was accomplished in 13 linear steps. Central to the synthetic approach was the diene-ene cross olefin metathesis reaction to generate the C6-C7 olefin without the use of protecting groups as the final step. Additional key reactions include

  FR901464 是一种有效的抗癌天然产物，可降低癌基因和肿瘤抑制基因的 mRNA 水平。在本文中，我们报告了 FR901464 的收敛对映选择性合成，该合成通过 13 个线性步骤完成。合成方法的核心是二烯-烯交叉烯烃复分解反应以生成 C6-C7 烯烃，而不使用保护基团作为最后一步。其他关键反应包括 Zr/Ag 促进的炔基化以设置 C4 立体中心、温和且化学选择性的 Red-Al 还原、试剂控制的立体选择性 Mislow-Evans 型 [2,3]-sigmatropic 重排以安装 C5 立体中心， Carreira 不对称炔基化生成 C4' 立体中心，以及高效的闭环复分解-烯丙基氧化序列以形成不饱和内酯。在生理相关条件下研究了 FR901464 右侧片段的分解途径。通过β-消除轻松打开环氧化物得到两个烯酮，其中一个可以通过其半缩酮脱水形成呋喃。为了防止这种分解途径，合理设计和合成了正确
• Oxyselenation of olefins by the use of aryl or alkyl selenocyanates and copper or nickel halides
  作者：Akio Toshimitsu、Sakae Uemura、Masaya Okano

  DOI：10.1039/c39770000166

  日期：——

  Reaction of olefins with aryl or alkyl selenocyanates in alcohol, water, or acetic acid in the presence of copper or nickel(II) halides produces the corresponding β-oxy selenides in high yields.

  在卤化铜或镍（II）的存在下，烯烃与芳基或烷基硒氰酸酯在醇，水或乙酸中的反应以高收率产生相应的β-氧硒化物。
• Sulfur-containing derivatives from (1R)-(−)-myrtenal designed as chiral ligands
  作者：Mariola Zielińska-Błajet、Paweł Rewucki、Szymon Walenczak

  DOI：10.1016/j.tet.2016.05.001

  日期：2016.7

  chiral sulfur-containing derivatives were prepared in the diastereoselective nucleophilic additions of thiophenols to the commercially available (1R)-(−)-myrtenal. The newly synthesized 3-phenylsulfanyl derivatives containing an aldehyde functionality were successfully transformed into enantiopure compounds with S, Se and N-donor atoms and applied as chiral ligands in palladium-catalyzed asymmetric allylic

  通过将硫酚的非对映选择性亲核加成反应制得新的手性含硫衍生物，所述苯酚是可商购的（1 R）-（-）-myrtenal。新合成的具有醛官能团的3-苯基硫烷基衍生物已成功转化为具有S，Se和N供体原子的对映体纯化合物，并作为手性配体应用于钯催化的不对称烯丙基烷基化反应（Tsuji–Trost反应），提供了对映异构体选择性高达到75％ee。

表征谱图